title: Light-induced O-glycosylation of unprotected deoxythioglycosyl donors.
abstract: The O-glycosylation of several unprotected deoxythioglycosides and alcohols using 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) under long-wavelength UV irradiation was effectively realized using a single electron transfer (SET) mechanism. In some cases, the use of p-methoxyboronic acid was very effective in temporary protection of the 1,3-diol (C4 and C6 positions) of the unprotected glycosyl donors to increase the yields of the obtained O-glycosides.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Yokohama 223-8522, Japan.
authors.forename: Mayuka
authors.initials: M
authors.lastname: Nakanishi
authors.forename: Daisuke
authors.initials: D
authors.lastname: Takahashi
authors.forename: Kazunobu
authors.initials: K
authors.lastname: Toshima
mesh_terms: D006031:Glycosylation; D008027:Light; D015394:Molecular Structure; D013862:Thiogalactosides / Q000737:chemistry*; D013863:Thioglucosides / Q000737:chemistry*
chemical_list: D013862:Thiogalactosides; D013863:Thioglucosides